HU186968B - Process for preparing cinnamoly-anthranilic acid derivatives substituted in the nucleus - Google Patents
Process for preparing cinnamoly-anthranilic acid derivatives substituted in the nucleus Download PDFInfo
- Publication number
- HU186968B HU186968B HU822794A HU279482A HU186968B HU 186968 B HU186968 B HU 186968B HU 822794 A HU822794 A HU 822794A HU 279482 A HU279482 A HU 279482A HU 186968 B HU186968 B HU 186968B
- Authority
- HU
- Hungary
- Prior art keywords
- anthranilic acid
- acid
- derivative
- cyclic amine
- formula
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 claims abstract description 32
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract description 21
- -1 cinnamoylanthranilic acid compound Chemical class 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- WJUFSDZVCOTFON-UHFFFAOYSA-N veratraldehyde Chemical compound COC1=CC=C(C=O)C=C1OC WJUFSDZVCOTFON-UHFFFAOYSA-N 0.000 claims abstract description 12
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims description 33
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 29
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 150000003935 benzaldehydes Chemical class 0.000 claims description 12
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 8
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 5
- IBGBGRVKPALMCQ-UHFFFAOYSA-N 3,4-dihydroxybenzaldehyde Chemical group OC1=CC=C(C=O)C=C1O IBGBGRVKPALMCQ-UHFFFAOYSA-N 0.000 claims description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 238000000354 decomposition reaction Methods 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- PCYGLFXKCBFGPC-UHFFFAOYSA-N 3,4-Dihydroxy hydroxymethyl benzene Natural products OCC1=CC=C(O)C(O)=C1 PCYGLFXKCBFGPC-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 2
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 claims description 2
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 claims description 2
- 235000012141 vanillin Nutrition 0.000 claims description 2
- VYSKLRHHFYJESB-UHFFFAOYSA-N 2-(3-phenylprop-2-enylamino)benzoic acid Chemical class OC(=O)C1=CC=CC=C1NCC=CC1=CC=CC=C1 VYSKLRHHFYJESB-UHFFFAOYSA-N 0.000 claims 1
- 239000003049 inorganic solvent Substances 0.000 claims 1
- 229910001867 inorganic solvent Inorganic materials 0.000 claims 1
- 125000000346 malonyl group Chemical group C(CC(=O)*)(=O)* 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 abstract description 6
- 239000000047 product Substances 0.000 abstract description 5
- NZHGWWWHIYHZNX-UHFFFAOYSA-N 2-((3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl)amino)benzoic acid Chemical compound C1=C(OC)C(OC)=CC=C1C=CC(=O)NC1=CC=CC=C1C(O)=O NZHGWWWHIYHZNX-UHFFFAOYSA-N 0.000 abstract description 3
- 239000002244 precipitate Substances 0.000 abstract description 3
- LZEMYXZYMHWMMN-UHFFFAOYSA-N 2-(phenylcarbamoyl)propanedioic acid Chemical compound OC(=O)C(C(O)=O)C(=O)NC1=CC=CC=C1 LZEMYXZYMHWMMN-UHFFFAOYSA-N 0.000 abstract 1
- 239000012445 acidic reagent Substances 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 12
- 238000001914 filtration Methods 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- GMEKUFJCKPYDAH-UHFFFAOYSA-N 2-(3-phenylprop-2-enoylamino)benzoic acid Chemical group OC(=O)C1=CC=CC=C1NC(=O)C=CC1=CC=CC=C1 GMEKUFJCKPYDAH-UHFFFAOYSA-N 0.000 description 9
- 239000013078 crystal Substances 0.000 description 8
- 238000000921 elemental analysis Methods 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 238000004566 IR spectroscopy Methods 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 description 4
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 208000024780 Urticaria Diseases 0.000 description 4
- 230000003266 anti-allergic effect Effects 0.000 description 4
- 208000006673 asthma Diseases 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- WMPDAIZRQDCGFH-UHFFFAOYSA-N 3-methoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1 WMPDAIZRQDCGFH-UHFFFAOYSA-N 0.000 description 3
- 206010012438 Dermatitis atopic Diseases 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 201000008937 atopic dermatitis Diseases 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- VFZRZRDOXPRTSC-UHFFFAOYSA-N 3,5-Dimethoxybenzaldehyde Chemical compound COC1=CC(OC)=CC(C=O)=C1 VFZRZRDOXPRTSC-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-O Piperidinium(1+) Chemical compound C1CC[NH2+]CC1 NQRYJNQNLNOLGT-UHFFFAOYSA-O 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- JVTZFYYHCGSXJV-UHFFFAOYSA-N isovanillin Chemical compound COC1=CC=C(C=O)C=C1O JVTZFYYHCGSXJV-UHFFFAOYSA-N 0.000 description 2
- JJVNINGBHGBWJH-UHFFFAOYSA-N ortho-vanillin Chemical compound COC1=CC=CC(C=O)=C1O JJVNINGBHGBWJH-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- NIVAFQOSMWPNDU-UHFFFAOYSA-N 2-[3-(3,4-dimethoxyphenyl)prop-2-enoylamino]benzoate;piperidin-1-ium Chemical compound C1CC[NH2+]CC1.C1=C(OC)C(OC)=CC=C1C=CC(=O)NC1=CC=CC=C1C([O-])=O NIVAFQOSMWPNDU-UHFFFAOYSA-N 0.000 description 1
- WIPMWRCUOVSCDQ-UHFFFAOYSA-N 3,5-diethoxybenzaldehyde Chemical compound CCOC1=CC(OCC)=CC(C=O)=C1 WIPMWRCUOVSCDQ-UHFFFAOYSA-N 0.000 description 1
- HAQLHRYUDBKTJG-UHFFFAOYSA-N 3,5-dihydroxybenzaldehyde Chemical compound OC1=CC(O)=CC(C=O)=C1 HAQLHRYUDBKTJG-UHFFFAOYSA-N 0.000 description 1
- DUCADUXTWKTAQE-UHFFFAOYSA-N 3,5-dipropoxybenzaldehyde Chemical compound CCCOC1=CC(OCCC)=CC(C=O)=C1 DUCADUXTWKTAQE-UHFFFAOYSA-N 0.000 description 1
- VAMZHXWLGRQSJS-UHFFFAOYSA-N 3-ethoxy-4-methoxybenzaldehyde Chemical compound CCOC1=CC(C=O)=CC=C1OC VAMZHXWLGRQSJS-UHFFFAOYSA-N 0.000 description 1
- QZMGMXBYJZVAJN-UHFFFAOYSA-N 3-ethoxybenzaldehyde Chemical compound CCOC1=CC=CC(C=O)=C1 QZMGMXBYJZVAJN-UHFFFAOYSA-N 0.000 description 1
- IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 description 1
- GFFJBSXKNZDYOJ-UHFFFAOYSA-N 3-propoxybenzaldehyde Chemical compound CCCOC1=CC=CC(C=O)=C1 GFFJBSXKNZDYOJ-UHFFFAOYSA-N 0.000 description 1
- VWQBRHFQINOZAI-UHFFFAOYSA-N 4-[3-(2-carboxyanilino)-3-oxoprop-1-enyl]-2-methoxyphenolate;piperidin-1-ium Chemical compound C1CC[NH2+]CC1.C1=C([O-])C(OC)=CC(C=CC(=O)NC=2C(=CC=CC=2)C(O)=O)=C1 VWQBRHFQINOZAI-UHFFFAOYSA-N 0.000 description 1
- JRHHJNMASOIRDS-UHFFFAOYSA-N 4-ethoxybenzaldehyde Chemical compound CCOC1=CC=C(C=O)C=C1 JRHHJNMASOIRDS-UHFFFAOYSA-N 0.000 description 1
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 1
- OQGTYVGUCWWYNK-UHFFFAOYSA-N 4-methoxy-3-propoxybenzaldehyde Chemical compound CCCOC1=CC(C=O)=CC=C1OC OQGTYVGUCWWYNK-UHFFFAOYSA-N 0.000 description 1
- FGXZWMCBNMMYPL-MSQIWANRSA-N 4-propoxybenzaldehyde Chemical compound CCCO[13C]1=[13CH][13CH]=[13C](C=O)[13CH]=[13CH]1 FGXZWMCBNMMYPL-MSQIWANRSA-N 0.000 description 1
- 206010003645 Atopy Diseases 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-O Pyrrolidinium ion Chemical compound C1CC[NH2+]C1 RWRDLPDLKQPQOW-UHFFFAOYSA-O 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- HUMNYLRZRPPJDN-KWCOIAHCSA-N benzaldehyde Chemical group O=[11CH]C1=CC=CC=C1 HUMNYLRZRPPJDN-KWCOIAHCSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-O morpholinium Chemical compound [H+].C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-O 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Dental Preparations (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56137344A JPS5838244A (ja) | 1981-09-01 | 1981-09-01 | 核置換シンナモイルアントラニル酸塩およびその製造方法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU186968B true HU186968B (en) | 1985-10-28 |
Family
ID=15196441
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU822794A HU186968B (en) | 1981-09-01 | 1982-08-31 | Process for preparing cinnamoly-anthranilic acid derivatives substituted in the nucleus |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US4486597A (en, 2012) |
| EP (1) | EP0074725B1 (en, 2012) |
| JP (1) | JPS5838244A (en, 2012) |
| AT (1) | ATE17115T1 (en, 2012) |
| AU (1) | AU562861B2 (en, 2012) |
| CA (1) | CA1189090A (en, 2012) |
| DE (1) | DE3268129D1 (en, 2012) |
| DK (1) | DK158467C (en, 2012) |
| ES (1) | ES8307208A1 (en, 2012) |
| FI (1) | FI75148C (en, 2012) |
| HU (1) | HU186968B (en, 2012) |
| NO (1) | NO159849C (en, 2012) |
| PT (1) | PT75452B (en, 2012) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4536346A (en) * | 1983-05-06 | 1985-08-20 | American Cyanamid Company | Aralkanamidophenyl compounds |
| JPS60214766A (ja) * | 1984-04-04 | 1985-10-28 | Terumo Corp | アミド誘導体およびこれを有効成分として含有する５−リポキシゲナ−ゼ作用阻害剤 |
| JPH0784424B2 (ja) * | 1987-04-15 | 1995-09-13 | 味の素株式会社 | チロシン誘導体及びその用途 |
| KR970006473B1 (ko) * | 1987-06-08 | 1997-04-28 | 오노 화아마슈티칼 캄파니 리미팃드 | 신나모일아미드 유도체, 그들의 제조방법, 그들을 함유하는 제약학적 조성물 및 그들의 사용 |
| WO2002055454A2 (en) * | 2001-01-10 | 2002-07-18 | Smithkline Beecham Corporation | Process and product |
| DE10208778B4 (de) * | 2002-02-28 | 2004-08-12 | Thyssenkrupp Stahl Ag | Aus Stahl-Hohlprofilen gebildete Tragstruktur für Fahrzeuge |
| DE10254872A1 (de) * | 2002-11-25 | 2004-06-03 | Symrise Gmbh & Co. Kg | Anthranilsäureamide und deren Derivate als kosmetische und pharmazeutische Wirkstoffe |
| NZ584613A (en) * | 2007-12-21 | 2011-07-29 | Fibrotech Therapeutics Pty Ltd | Halogenated cinnamoylbenzamide derivatives for anti-fibrotic drugs |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3755603A (en) * | 1970-07-01 | 1973-08-28 | Syntex Corp | Biphenylyloxyacetic acids in pharmaceutical compositions |
| JPS5640710B2 (en, 2012) * | 1973-01-18 | 1981-09-22 | ||
| JPS511440A (ja) * | 1974-04-18 | 1976-01-08 | Kissei Pharmaceutical | Shinkihokozokukarubonsanjudotai no seizohoho |
| JPS5848545B2 (ja) * | 1974-04-18 | 1983-10-28 | キツセイヤクヒンコウギヨウ カブシキガイシヤ | シンキホウコウゾクカルボンサンアミドユウドウタイ ノ セイゾウホウホウ |
| US4337270A (en) * | 1980-05-21 | 1982-06-29 | Hisamitsu Pharmaceutical Co., Inc. | Novel anthranilic acid derivatives |
| JPS568858A (en) * | 1980-06-23 | 1981-01-29 | Hitachi Ltd | Resin sealing type semiconductor device |
-
1981
- 1981-09-01 JP JP56137344A patent/JPS5838244A/ja active Granted
-
1982
- 1982-08-13 AU AU87148/82A patent/AU562861B2/en not_active Expired
- 1982-08-19 EP EP82304389A patent/EP0074725B1/en not_active Expired
- 1982-08-19 DE DE8282304389T patent/DE3268129D1/de not_active Expired
- 1982-08-19 AT AT82304389T patent/ATE17115T1/de not_active IP Right Cessation
- 1982-08-23 PT PT75452A patent/PT75452B/pt not_active IP Right Cessation
- 1982-08-25 FI FI822953A patent/FI75148C/fi not_active IP Right Cessation
- 1982-08-26 CA CA000410210A patent/CA1189090A/en not_active Expired
- 1982-08-31 DK DK389582A patent/DK158467C/da not_active IP Right Cessation
- 1982-08-31 HU HU822794A patent/HU186968B/hu unknown
- 1982-08-31 ES ES515401A patent/ES8307208A1/es not_active Expired
- 1982-08-31 NO NO822943A patent/NO159849C/no not_active IP Right Cessation
-
1984
- 1984-02-07 US US06/577,758 patent/US4486597A/en not_active Expired - Lifetime
- 1984-08-14 US US06/640,588 patent/US4623724A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| NO822943L (no) | 1983-03-02 |
| NO159849B (no) | 1988-11-07 |
| PT75452B (en) | 1984-11-19 |
| DK158467B (da) | 1990-05-21 |
| EP0074725B1 (en) | 1985-12-27 |
| EP0074725A1 (en) | 1983-03-23 |
| ES515401A0 (es) | 1983-07-01 |
| US4486597A (en) | 1984-12-04 |
| FI822953A0 (fi) | 1982-08-25 |
| ES8307208A1 (es) | 1983-07-01 |
| FI75148C (fi) | 1988-05-09 |
| DK158467C (da) | 1990-10-22 |
| FI822953L (fi) | 1983-03-02 |
| JPS5838244A (ja) | 1983-03-05 |
| ATE17115T1 (de) | 1986-01-15 |
| NO159849C (no) | 1989-02-15 |
| US4623724A (en) | 1986-11-18 |
| AU562861B2 (en) | 1987-06-18 |
| AU8714882A (en) | 1983-03-10 |
| PT75452A (en) | 1982-09-01 |
| FI75148B (fi) | 1988-01-29 |
| JPH0136462B2 (en, 2012) | 1989-07-31 |
| CA1189090A (en) | 1985-06-18 |
| DE3268129D1 (en) | 1986-02-06 |
| DK389582A (da) | 1983-03-02 |
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| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 |